Acetic Acid → HCID 13151266, compound

HRID 344595

Reaction equation

HRID 344595 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([C:9]([F:13])=[CH:10][C:11]=1[Cl:12])[NH2:8])[CH:2]=[CH2:3].[CH2:14]1[CH:19]2[C:20]([O:22][C:23](=O)[CH:18]2[CH2:17][CH:16]=[CH:15]1)=[O:21].C(O)(=O)C>O>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([N:8]2[C:20](=[O:21])[C:19]3[CH2:14][CH2:15][CH2:16][CH2:17][C:18]=3[C:23]2=[O:22])[C:9]([F:13])=[CH:10][C:11]=1[Cl:12])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6810Tetrahydrophthalic anhydrideHCID 132729264-Chloro-2-fluoro-5-[(prop-2-en-1-yl)oxy]aniline

Product 1

HCID 13151266HCID 13151266, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 9.0 g of 19A, 6.8 g of THPA and 100 mL of glacial acetic acid was heated at reflux temperature for 4 hours. The resulting mixture was cooled to room temperature, poured into 450 mL of water and extracted with ether. The extract phase was washed with water, dried (Na2SO4), and filtered, and the solvent was evaporated from the filtrate. The residue was flash-chromatographed on silica gel, with a 15:85 v:v mixture of ethyl acetate and hexane as eluent, to give N-(3-(allyloxy)-4-chloro-6-fluorophenyl)-3,4,5,6-tetrahydrophthalimide (19B), as an orange oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 4 hours
  3. extractionextracted with ether
  4. washThe extract phase was washed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated from the filtrate
  8. customThe residue was flash-chromatographed on silica gel, with a 15:85 v
  9. additionv mixture of ethyl acetate and hexane as eluent

Sources & evidence

ORD record
ord-c5c913faacfa489ca53cd32ebd138158
Source dataset
uspto-grants-1991_10
Patent number
US05053071

Linked notes

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